A deer on a road with vegetation on the sides.

Search Vacation Homes in Ashland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Ashland vacation homes

Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, WiFi (free)

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is ￥20,546
￥43,435 total
includes taxes & fees
Sep 1 - Sep 2
Barclay Klum House by WanderLodges
Smart TV

2. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (52 reviews)
"The bungalow was great. Every room was comfortable and efficient for what we needed. The location is perfect...quiet yet easy walk to anywhere downtown. We would stay here again!!"
United States
Amy R.
The price is ￥16,137
￥35,844 total
includes taxes & fees
Sep 9 - Sep 10
East Main Downtown Bungalow
Grand House | Living area | 65-inch TV with digital channels, streaming services

3. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is ￥27,366
￥53,718 total
includes taxes & fees
Sep 7 - Sep 8
The Mountain Ave House by WanderLodges
Sundeck

4. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
The price is ￥30,417
￥63,209 total
includes taxes & fees
Sep 14 - Sep 15
Grandview of Ashland
Interior detail

5. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private."
United States
David
The price is ￥27,223
￥42,671 total
includes taxes & fees
Sep 10 - Sep 11
Hanna's House by WanderLodges
Interior

6. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is ￥36,661
￥67,473 total
includes taxes & fees
Sep 1 - Sep 2
Savage Upon Siskiyou
Smart TV

7. Hanna`s House | Downtown Retreat, Steps to OSF

Hanna`s House | Downtown Retreat, Steps to OSF
Historic Railroad District
10.0 out of 10, Exceptional, (170 reviews)
"Excellent quaint cottage….great location….easy check in….very well stocked and very comfortable….second year at this cottage and will be back next year!!"
United States
Jim L.
The price is ￥26,239
￥48,492 total
includes taxes & fees
Sep 10 - Sep 11
Hanna`s House | Downtown Retreat, Steps to OSF
Smart TV

8. Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Ashland
10.0 out of 10, Exceptional, (5 reviews)
"Lovely stay in a nicely restored historic home. We were very comfortable and the location is great in central Ashland."
United States
Casey K.
The price is ￥22,717
￥53,376 total
includes taxes & fees
Aug 31 - Sep 1
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Exterior

9. Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.8 out of 10, Exceptional, (10 reviews)
"Loved loved loved staying here and had a fantastic stay with very reasonable rates! It is a bit difficult to find where the apartment was, but once we figured that part out, everything fell right into place. Huge thank you to the hosts for their excellent and timely communication- I also was a huge fan of the easy check in and check out process. Views are spectacular in this area and make for a really special and beautiful stay."
United States
Cameron A.
The price is ￥28,672
￥40,477 total
includes taxes & fees
Aug 31 - Sep 1
Chateau Herb ~ Miranda Carriage House Apt
Outdoor dining

10. Swank Suites | King with Lux Tub

Swank Suites | King with Lux Tub
Historic Railroad District
9.8 out of 10, Exceptional, (8 reviews)
"Excellent…well thought out, attention to detail, comfortable, clean and friendly staff!Would definitely stay here again!"
United States
Susie P.
The price is ￥24,334
￥31,059 total
includes taxes & fees
Aug 31 - Sep 1
Swank Suites | King with Lux Tub
Exterior

11. Downtown Ashland House - Walk to Plaza and OSF!

Downtown Ashland House - Walk to Plaza and OSF!
Ashland
9.8 out of 10, Exceptional, (46 reviews)
"Great place to stay and so close to shops and restaurants. "
United States
Jeff C.
The price is ￥24,974
￥63,807 total
includes taxes & fees
Sep 7 - Sep 8
Downtown Ashland House - Walk to Plaza and OSF!
Coffee/tea maker, fridge, microwave, oven

12. Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (69 reviews)
"The property was very pleasant and clean... great directions to get to it, friendly host, sweet outdoor space, clean and welcoming. "
United States
Sue P.
The price is ￥29,617
￥52,836 total
includes taxes & fees
Sep 6 - Sep 7
Quiet and peaceful cottage close to downtown
Exterior

13. Whimsy on B | The Studio

Whimsy on B | The Studio
Historic Railroad District
The price is ￥19,195
￥35,234 total
includes taxes & fees
Aug 31 - Sep 1
Whimsy on B | The Studio
Coffee/tea maker, fridge, microwave, oven

14. Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Ashland
9.8 out of 10, Exceptional, (76 reviews)
"Nice spot close to downtown and OSF."
United States
Matthew
The price is ￥32,562
￥82,360 total
includes taxes & fees
Sep 7 - Sep 8
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Interior

15. The Ashland Social | Main House

The Ashland Social | Main House
Ashland
10.0 out of 10, Exceptional, (35 reviews)
"Home is beautiful and well-located in Ashland. Amenities were great, and having three en-suite bedrooms was perfect. Host communicated well and often to ensure trouble-free experience. Fully equipped kitchen ideal for anyone to enjoy.We highly recommend this property!"
United States
Paul B.
The price is ￥58,433
￥125,953 total
includes taxes & fees
Sep 28 - Sep 29
The Ashland Social | Main House
Exterior

16. Whimsy on B | 2BR Steps to Downtown

Whimsy on B | 2BR Steps to Downtown
Historic Railroad District
The price is ￥24,478
￥48,255 total
includes taxes & fees
Aug 31 - Sep 1
Whimsy on B | 2BR Steps to Downtown
1 bedroom, WiFi, bed sheets

17. Moody Ashland Escape: Luxe Suite, Copper Tub

Moody Ashland Escape: Luxe Suite, Copper Tub
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our overnight stay. The place is centrally located, easy walking distance to downtown, and cozy. We loved the heated bathroom floors and the decor. Nice off street parking. Highly recommend. "
United States
Jon W.
Moody Ashland Escape: Luxe Suite, Copper Tub
Terrace/patio

18. Come Stroll-inn in Downtown Ashland

Come Stroll-inn in Downtown Ashland
Siskiyou-Hargadine Historic District
The price is ￥36,020
￥72,472 total
includes taxes & fees
Sep 4 - Sep 5
Come Stroll-inn in Downtown Ashland
Property grounds

19. Charming house two blocks from downtown Ashland

Charming house two blocks from downtown Ashland
Historic Railroad District
9.6 out of 10, Exceptional, (12 reviews)
"This is our favorite spot to stay in Ashland! The location is perfect for walking downtown to the shops and theaters, shopping at the local co-op, or just enjoying a sunny breakfast on the deck."
United States
Julia W.
Charming house two blocks from downtown Ashland
Outdoor dining

20. Hot tub | Sauna |Firepit |Sleeps 6!

Hot tub | Sauna |Firepit |Sleeps 6!
Ashland
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely stunning property in the hills of Ashland!"
United States
Heather K.
The price is ￥33,283
￥76,687 total
includes taxes & fees
Sep 13 - Sep 14
Hot tub | Sauna |Firepit |Sleeps 6!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

10/10 Excellent
"Nice hotel and walking distance to shopping and restaurants"
Dawn 1-night trip
Posted 3 hours ago
The Bard's Inn, BW Signature Collection by Best Western

Find out more about Ashland

Ashland Vacation Homes information

Number of reviews
519
Accommodation
273 Vacation Homes
Lowest Price
￥31,059
Highest Price
￥125,953